Director, Enterprise Customer Success

LearnUpon • Full-time • Hybrid in Philadelphia, Pennsylvania, United States • 1d ago

Fast Facts

LearnUpon is seeking a Director of Enterprise Customer Success in Philadelphia, PA, to enhance customer retention and drive measurable business outcomes for enterprise clients through effective leadership and strategic collaboration.

Responsibilities: Oversee customer engagement frameworks, drive revenue retention, design onboarding strategies, and lead a high-performing team to ensure customer success and scalability.

Skills: 5+ years in Customer Success or Professional Services in a SaaS environment, strong financial acumen, leadership presence, and proficiency in CRM platforms.

Qualifications: Experience in edtech or LMS platforms and building enterprise CX models are a plus, but not mandatory.

Location: This is a hybrid role based in Philadelphia, PA, requiring at least one day per week in the office.

Compensation: Not provided by employer. Typical compensation ranges for this position are between $130,000 - $180,000.

LearnUpon is looking for a Director of Enterprise Customer Success to join our team in Pennsylvania. This is a hybrid role, working one or more days per week from LearnUpon's Philadelphia City office.

LearnUpon LMS helps organizations train their employees, partners, and customers. Businesses can manage, track, and achieve their unique learning goals — all through a single, powerful solution.

With offices in Dublin (our HQ), Belgrade, Philadelphia, Salt Lake City, London and Sydney, we are a global team with lots of diverse cultures, backgrounds, and experiences that puts our customers' experience at the heart of everything we do. Our culture fosters an open, collaborative and supportive environment where our accomplishments are celebrated and encouraged. We're always striving for the best solution (not the easy one). We’re proud of our success and we’re humble and hungry to achieve more.

The Customer Success (CS) organization at LearnUpon is evolving to drive global scale, predictability, and long-term customer value.

The Director, Enterprise Customer Success owns the retention, renewal readiness, and long-term value realization of LearnUpon’s Enterprise customer segment. This leader is responsible for operating a predictable, scalable, and commercially aligned Enterprise CX model that delivers measurable business outcomes for customers and strong Gross and Net Revenue Retention for LearnUpon. This role oversees leaders, and individual contributors across Enterprise Customer Success, Implementation, and Solutions Architecture, and serves as a key partner to Sales, Product, Finance, and Operations.

What will I be doing?

Own the Enterprise CS operating model, engagement frameworks, and playbooks to ensure scalable, high-impact customer journeys.
Drive Gross and Net Revenue Retention through proactive risk management and accurate renewal forecasting.
Design onboarding and success motions that accelerate time-to-value and demonstrate measurable ROI for complex accounts.
Collaborate with Sales to identify and secure expansion opportunities grounded in proven customer success.
Recruit, mentor, and scale a high-performing team, fostering commercial acumen and operational excellence.
Partner with CS Ops to define capacity models, account ratios, and the tooling required for Enterprise scale.
Define and monitor key Enterprise KPIs to optimize team performance and identify trends in customer health.
Serve as the "Voice of the Enterprise Customer" to internal Product and R&D teams to influence the roadmap.
Act as the lead executive point of contact for high-stakes customer situations and resolution strategies.
Navigate ambiguity with decisive judgment, balancing empathy with high accountability to drive organizational clarity.

What skills do I need?

5+ years leading Customer Success, Professional Services, or Implementation teams in a SaaS environment.
Proven experience owning or materially influencing retention, renewals, and commercial outcomes.
Experience leading managers and multi-layered organizations.
Strong business and financial acumen, with comfort operating against retention and renewal targets.
Leadership presence and confidence engaging with C-suite stakeholders.
Demonstrated ability to lead teams through change and scale.
Experience operating across multiple regions and time zones.
Proficiency with CRM and CS platforms (e.g. Salesforce, Planhat, Gainsight, etc.)

Not required but considered a big plus

Experience in learning, edtech, or LMS platforms
Experience building or evolving enterprise-scale CX operating models

Don’t worry if you don’t tick every box in order to apply, we’re always happy to review applications and take all experience into consideration. We do our best to provide feedback where we can!

Why work with us?

Competitive salary and company ESOP.
Comprehensive private health insurance scheme and 401k.
25 days annual leave + 1 annual company wellness day off.
Work in a fun and supportive environment with regular team events.
Structured learning and development opportunities

What is the Hiring Process?

Our typical process generally works as follows:

Qualified applicants will be invited to schedule a screening call.
Successful candidates will then be invited to a series of practical interviews.
Finally, candidates will have a short interview with a member of our C-Suite Team.
The successful candidate will be contacted with an offer to join our team.

LearnUpon is an Equal Opportunities Employer.

We do not discriminate on the basis of gender, marital status, family status, age disability, sexual orientation, race, religion, membership of the Traveller community, or any other legally protected status.

By applying for this job, you agree to LearnUpon's Privacy Policy. Find out more about our privacy policy here

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